Date: Sat, 15 Jul 2017 06:35:25 -0400
From: Jaye Dee Bowman
Subject: The Joys of Crossdressing
THE JOYS OF BEING A CROSSDRESSER
I have been crossdressing almost all of my life. It all started one day
innocently enough by my being curious about what a female would wear, how
it would feel and how I would look. I had come home from school a little
early and discovered that my mom wasn't home, she had gone shopping with
her sister, my aunt. I then went into my moms bedroom and went straight for
her large dresser. I opened the top right hand draw and found stockings,
all neatly folded. I took out the very last pair and just held them in my
hand and felt that wonderful wispy feel that only a full fashioned nylon
stocking can feel like. I must have held that pair of stockings for a while
and then decided to try to put them on. I took off all my clothes in record
time and was standing there totally naked. I sat down on my moms bed and
separated the stockings and crossed my legs and started to roll up one of
the stockings so I could slid it up my leg. I had caught my older cousin
doing this so I had a clue as to what to do. My older cousin was a girl
about 4 years older then me and to be honest, she was HOT. So, here I was
sliding this stocking up my right leg. The feeling was electric, I then did
the same thing on my left leg. I'm standing in front of the full length
mirror and thinking how am I going to keep these stockings on. I then
reached into the top left hand draw and came out with a garter belt. I had
no idea as to how this thing went on but I figured out quickly. As soon as
the garter belt was on I started to attach the garters to the tops of the
stockings. It took a while but I caught on quickly. I am now looking in the
full length mirror again with the erect penis sticking straight out. I
figured I had to hid it so I opened another dresser draw and removed a pair
of silk panties. I slid them up my nylon legs and fitted them onto my ass
and my "boy bits". The feeling was amazing. At this point my mom comes home
and calls me. I'm in her room wearing a pair of stockings, a garter belt
and panties and no where to run. She now walks into her bedroom and sees me
standing there. At first she is totally shocked to see me this way. She
sits down on her bed and looks at me and asks me what am I doing. I am now
nervous as a cat and really don't know what to say. So I just tell her that
I'm soooo sorry for this to happen and it will never happen again, I start
to slide the panties down my legs when she says to stop. She motions for me
to sit next to her which I do. Mom then asks me why didn't I ask her
permission to try on her lingerie first. I just looked at her with this
"are you kidding me kinda' look". Mom then asks me if I want to really see
what I would look like dressed as a girl. I just nod my head yes, she then
gets up and goes to her closet and gets a pencil skirt, a blouse and high
heels. She also gets a wig from the back of her closet and she then tells
me to finish getting dressed and then she will help me with the wig. I am
speechless, I mean totally speechless. I do as she asks and when I am
finished getting dressed she puts the wig on my head and adjusts it. I have
slipped into the high heels which btw are just a little to big but fit OK
for now. Mom then has me sit at her vanity table and does my face. When she
has finished she tells me to look in the mirror. I am shocked and I mean
shocked to see a pretty girl looking back at me. Mom says that I look like
my older cousin Janice and I do.
I don't know if mom had an idea that if she made me into a girl that I
would never dress up again. Mom then said to me that for the rest of day I
was to stay dressed as a girl. Mom showed me how to walk in high heels
which I mastered quickly and impressed her. I helped her put her new items
of clothing away and she then told me that everything that I had on was now
mine. She also told that she wants to see me dressed as a girl whenever we
are alone. She also told me that she was willing to take me shopping for my
own wardrobe if and when I wanted to stay dressed all the time.
It didn't take me long to discover that I wanted to be a girl. I actually
hated being a boy and I guess mom helped me by putting all sorts of
positive thoughts into my head when we spoke as opposed to being a
boy. Just the thought of wearing soft, silky things, having a nice chest
that gets looked at, wearing nylons, hearing the high heels clicking on the
floor, wearing makeup and having your hair done. All the things that make a
girl a woman.
When I turned 17, mom asked me a very important question. She wanted to
know if I REALLY wanted to become a girl. There was no hesitation in my
response and I said YES YES YES. Mom then made some phone calls and I was
scheduled for medical exams to become a female. At the end of almost 9
months I had all the surgeries needed to be a real woman. I had nice full C
cup breasts, a vagina that could accommodate a 8 inch penis. Mom showed me
how to give a man real good "head" and how to receive a lubricated penis
into my vagina. I really love it when a man is pumping his cock into me and
I feel him cumming. But there have been times when I prefer having that
cock in my mouth so I can taste and swallow that massive load of semen.
I thank my mother everyday for helping me go from being a crossdresser to a
woman. I have never looked backwards that once I was a boy. I met a guy at
work one day and we hit it off right from the beginning. We became an item
very shortly thereafter. I guess we were together for almost 3 months when
Michael sat me down and looked me in the eye and said that he had a secret
that he has to share with me. I reached out and held both his hands and
discovered that his hands were as soft as mine and that he had clear nail
polish on them. Not that this sort of thing was uncommon, actually it was
very common. He looked me in the eye, cleared his throat and then told me
that on occasion he likes to dress as a woman. I just looked at him and
smiled and told him that it was alright with me and that I wanted to see
him dressed. He asked me if today would be ok with me. I smiled and nodded
my head yes. We went to his apartment and he asked me to give him about an
hour or so. I said sure, take all the time you need. I sat on the couch,
crossed my nylon legs and waited. In about 1 hour and a half I heard a pair
of heels walking down the hall. I took a deep breath not knowing as to what
I was going to see. Michael then walked into the living room, an absolute
picture of femininity. I got up and walked over to "her" with this smile on
my face and kissed "her" tenderly telling "her" how beautiful she looked.
After I did a complete 360 on "her" I just had to kiss "her" and when I did
the "animal passion" took control; of both of us. My hands roamed all over
her body and settled on the cheeks of her ass. This enabled me to do two
things, squeeze her fine looking ass and to pull her as close as I could
into me. Michelle as she is now called did the same to me. Looking at us
you would swear that we are 2 lesbians and to some extent you would be
right. We both sat down on the couch and looked at each other. At this
point I told Michelle that I want her dressed this way all the time. She
just looked at me with this bewildered look and asked why. I then told her
the story of my life. After that, we had a drink or two or three and
started loving each other the way 2 women would. I told her I wanted her to
become a real girl, like me and she said that she would REALLY consider
it. Well it didn't take long for Michelle to make up her mind and now she
is an "honest injin girl" like me.
Crossdressing can lead you in so many different directions, but the
direction that it lead me was into womanhood. Even with all the disparities
between male and female pay scale and other significant things I much
prefer to be a woman.